Discussion Guide: Messy-middle Moments

PRAYER

Our goal today is to grow in relationship and learn how to walk with one another in all God has called us to be and do. Let’s begin by praying for each other.

Does anyone have prayer requests or stories of how God has been moving in your life that we can celebrate together?

THE SECOND CHANCES TOPIC

PAUL, MESSY-MIDDLE

THIS WEEK

We’re starting a new series from the book of Epistle to Philemon called Second Chances: A Path to Making What’s Broken Beautifully Whole, Again. Over the next few weeks, we’ll discover how the gospel works through real relationships—bringing reconciliation, restoration, and transformation where brokenness once defined the story.

This week, Pastor Alvin invites us into a moment where Paul the Apostle found himself penning a heartfelt letter in a messy middle—standing between two people, helping them move toward healing through the power of the gospel.

To help us start our time together, consider these questions (CHOOSE ONE, and don’t feel obliged to use any or all of them):

Share about a time when you found yourself “in the middle” of a conflict (either your own or between others). What made it difficult?

When conflict happens, do you naturally avoid it, confront it, or try to mediate it? Why?

What qualities make someone a good peacemaker?

How have you seen faith influence the way someone handled a difficult relationship?

DISCUSSION QUESTIONS

SCRIPTURE

Have someone read Philemon 1:1-25 aloud. As you listen, notice any words or phrases that stand out, and ask the Holy Spirit to highlight something for you.

Philemon 1:1-25
1 Paul, a prisoner for Christ Jesus, and Timothy our brother,

To Philemon our beloved fellow worker 2 and Apphia our sister and Archippus our fellow soldier, and the church in your house:

3 Grace to you and peace from God our Father and the Lord Jesus Christ.

Philemon's Love and Faith
4 I thank my God always when I remember you in my prayers, 5 because I hear of your love and of the faith that you have toward the Lord Jesus and for all the saints, 6 and I pray that the sharing of your faith may become effective for the full knowledge of every good thing that is in us for the sake of Christ.[a] 7 For I have derived much joy and comfort from your love, my brother, because the hearts of the saints have been refreshed through you.

Paul's Plea for Onesimus
8 Accordingly, though I am bold enough in Christ to command you to do what is required, 9 yet for love's sake I prefer to appeal to you—I, Paul, an old man and now a prisoner also for Christ Jesus— 10 I appeal to you for my child, Onesimus,[b] whose father I became in my imprisonment. 11 (Formerly he was useless to you, but now he is indeed useful to you and to me.) 12 I am sending him back to you, sending my very heart. 13 I would have been glad to keep him with me, in order that he might serve me on your behalf during my imprisonment for the gospel, 14 but I preferred to do nothing without your consent in order that your goodness might not be by compulsion but of your own accord. 15 For this perhaps is why he was parted from you for a while, that you might have him back forever, 16 no longer as a bondservant[c] but more than a bondservant, as a beloved brother—especially to me, but how much more to you, both in the flesh and in the Lord.

17 So if you consider me your partner, receive him as you would receive me. 18 If he has wronged you at all, or owes you anything, charge that to my account. 19 I, Paul, write this with my own hand: I will repay it—to say nothing of your owing me even your own self. 20 Yes, brother, I want some benefit from you in the Lord. Refresh my heart in Christ.

21 Confident of your obedience, I write to you, knowing that you will do even more than I say. 22 At the same time, prepare a guest room for me, for I am hoping that through your prayers I will be graciously given to you.

Final Greetings
23 Epaphras, my fellow prisoner in Christ Jesus, sends greetings to you, 24 and so do Mark, Aristarchus, Demas, and Luke, my fellow workers.

25 The grace of the Lord Jesus Christ be with your spirit.

Paul Entered the Messy Middle with Gospel Identity

In the opening of the letter, Paul prayerfully approached the conflict with humility, identifying himself as a “prisoner of Christ” rather than appealing to his authority as an apostle. Instead of confronting the issue immediately, he first affirmed the faith and love of Philemon, recognizing the evidence of God’s work already present in his life. By doing this, Paul set a tone shaped by grace rather than pressure. He also reminded everyone that the gospel does more than save individuals—it creates a new spiritual family where relationships matter and reconciliation reflects the transforming power of Christ.

Leader Note:
Paul didn’t start with prayerless correction—he started with identity steeped in prayer.
Remembering our identity in Jesus Christ shifts our focus from being right to being rightly reconciled to God and others respectively. Because we’ve received grace, we’re able to approach conflict with humility, forgiveness, and a desire for restoration. When we know who we are in Jesus, love becomes the natural outflow.

Where in your daily life—where you live, work, and play—is God inviting you to lead with grace and encouragement instead of frustration or correction?

How might remembering the grace you’ve received shape the tone of your next difficult conversation?

What truths about your identity in Christ do you need to remember as you navigate relational tension?

What practical step could you take toward reconciliation instead of simply proving a point?

Paul Stepped Into the Gap for Transformation

In verses 8–16, Paul the Apostle stepped into the messy middle with a posture of love and patience, choosing to appeal rather than command. He could have used his apostolic authority to enforce obedience, but instead he invited a voluntary response, trusting that grace—not pressure—would guide the outcome. This shows that transformation often begins with relational trust, not force, and that approaching conflict with humility opens the door for hearts to change.

Beyond appealing to Philemon, Paul also invested deeply in Onesimus’ growth. He discipled him after his conversion, helping him embrace a new identity in Christ. Paul reframed Onesimus from “useless” to “useful” and from slave to brother, demonstrating that the gospel doesn’t just forgive—it restores and redefines. By stepping into the gap in this way, Paul modeled how love and intentional guidance can bring lasting transformation, turning a broken situation into an opportunity for reconciliation and spiritual growth.

Leader Note:
Point 1 focuses on our posture in conflict, reminding us to lead with humility and our identity in Christ before addressing the situation. Point 2 shifts to our actions toward others, showing how we can step into the gap with love, guidance, and intentional investment to help bring transformation and restoration. Discipleship opportunity.

What does it look like for you to invest relationally in someone’s growth, rather than just giving advice or correction?

How can you approach a difficult relationship with love and patience instead of trying to control the outcome?

Who in your life might need your guidance or support to embrace a new identity and journey in Christ? 

How can you create trust in a broken relationship so that transformation can take place naturally?

Paul Absorbed the Cost of Reconciliation

In verses 17–25, Paul the Apostle demonstrated what it means to absorb the cost of reconciliation. He offered to take on Onesimus’ debt, stepping in as a mediator between two broken parties and personally shouldering the responsibility to restore the relationship. By doing so, Paul modeled the gospel in action—showing that true reconciliation often requires sacrifice, selflessness, and a willingness to bear the cost so that others can experience restoration and unity.

Paul demonstrated what reconciliation actually costs. This mirrors what Jesus ultimately did on the cross—absorbing our debt to reconcile us to God.

How can you step into a situation to help restore a relationship like Paul, with the goal of leading them to Jesus?

How can you reflect Christ’s example of bearing cost in a way that points someone to the gospel?

What would it look like for reconciliation to become part of your evangelism?

In what ways could your willingness to absorb relational cost open the door for someone to see and respond to Jesus?

CLOSING THOUGHT

Paul shows us that evangelism is more than just sharing words—it’s action stepping into messy, broken situations so others can experience reconciliation and the transforming power of the gospel. We see this reflected in restored identity, transformed lives, and debts absorbed, all pointing to Jesus, the true Mediator. As you reflect on your own life, consider how might God be sending you to be like Paul, being called to step in and mediate? The challenge for each of us is to take action this week—let the grace you’ve received motivate you to engage in a relationship where you can reflect Christ’s love, bring healing, and open the door for someone to encounter Jesus through your words and deeds.

Let’s close in prayer: Lord, thank You for the grace we have received through Jesus Christ, who stepped into the gap to reconcile us to You. Help us remember our identity in Him and give us humility, courage, and love to step into the messy middle of broken relationships. Teach us to be peacemakers who reflect the gospel in our daily lives, so that others may see Your transforming grace and be drawn to You. Amen.